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“It’s down the tubes, totally,” said the dejected record exec on the phone, describing his business. Standard sentiments to be sure, but this time from an unexpected source: Scorpio, one of the last remaining music bootleggers in the country, calling from an undisclosed bunker in the New York area.

The music industry took another tumble in 2009, with CD sales down 12.7 percent from 2008. But the shadier, shadowy side of the business has been equally decimated. At one time, as many as 75 unofficial bootleg “companies” existed, illegally cranking out LPs and then CDs of hard-to-find studio and soundboard-jacked live recordings by the Beatles, Bob Dylan, Phish, Pearl Jam, and other rock icons. Some, like the multidisc Dylan Ten of Swords box, are considered classics. Although it’s impossible to gauge exactly how profitable this quasi-industry was, the four-decade-old bootlegging biz generated millions of dollars globally. But now, this old-school method of illegal music distribution — one of rock’s most illustrious if illicit traditions — is being destroyed right along with the legit CD, all by the new-school method: the Internet.

Just ask Scorpio. (Which, of course, isn’t his real name. Like a rock-and-roll Deep Throat, he prefers to use the name of his own longtime label; after a message is relayed to him, he calls from a number that comes up blocked.) Scorpio began cranking out boots (of rare Sex Pistols or New York Dolls songs) in the late seventies, selling them to record stores both in the city and beyond. “I always wanted to get a job at a record company, but nobody would hire me,” he says. “The reason I did a collection of Dolls demos was because I was a fan and I wanted one.” He won’t say how much he made during his peak years (and record stores who still carry them decline comment, not surprisingly). But by the nineties, he was selling as many as 10,000 copies of “hits” like a Misfits collection. He earned enough to quit his day job (“restaurant delivery and bars”) and live full time off his side vocation. “I made what a good used car salesman might make,” he says. “I could afford to go overseas and stay in a decent hotel. It was a reasonable business for a while.”

The beginning of the end arrived in two shifts. First came the advent of the affordable CD-R recorder in the mid-nineties. Scorpio would visit Village record stores and find dubbed copies of his own records. “It got hard to distinguish the real product from the knockoffs,” he gripes. “There are a lot of lowlifes and scumbags in this business — if you want to disparage the term ‘scumbag.’” Then came the Internet, where easily accessible — and free — downloads of concert tapes are, to use the name of one such site that doles them out, a Dime a Dozen. “This is about hobbyists who are not doing it for money,” says Jeff, one recordings poster who doesn’t charge. “Fans want to share their recordings. They don’t want them to go to some bootlegger. You make a better world through giving.”

Here in the States, Scorpio embodies the collapse of his underworld industry. In the old days, a “smash” bootleg could sell between 5,000 and 10,000 units, which someone like Scorpio could sell for as much as $50 (minus costs for elaborate booklets and photo reproduction, which could be considerable in Scorpio’s case). But Scorpio’s recent three-CD David Bowie set, Secrets of My Lost Years 1969–1973 (demos, studio outtakes, and tapes from TV appearances, all from Bowie’s pre-stardom era), took Scorpio four years to compile and has only sold 300 copies in the few stores that carry it. Asked how many new boots he produces a year, Scorpio says, over the phone, “I’m raising one finger on one hand.” As a result, Scorpio has returned to construction work, and any rare collection he now assembles (like long-rumored 1969 Boston live tapes of the Velvet Underground) is, he says, “an accent to the daily grind.” Plus, he adds, the music itself is now less interesting: “Do you really need outtakes of the Verve?”

Mourn or laugh if you like — it’s hard to feel too bad for these guys, who were the ones ripping off the labels and artists before the Internet, just not as successfully — but the demise of the bootleg industry should serve as yet another chilling omen for actual record companies. “The moment [a new bootleg] is released, it ends up on a website and people get it for free,” says Erik Flannigan, who wrote a bootleg column for the now-defunct music newsletter ICE. Fans refusing to pay for music, opting to trade it online and thereby bankrupt the companies that were selling it: Sound familiar?